Leadoff, no question about it, it’s not often you find someone who offers everything you could want in a leadoff hitter: Power, Speed, Patience, and he wants to hit there. Let Pedroia, Crawford, or Agon hit 3rd

I think third because he is  hitting 32 hrs and 105 rbis. That is good.

Rickey Henderson hit for power, but was nearly always a lead-off hitter. Sure, Rickey would have gotten more RBI as a #3, but his speed and on-base presence made it imperative that he remained the lead off hitter. That is where Ellsbury belongs, regardless of his power.

1 Crawford
2 Pedey
3 Ells
4 Adrian
5 Youk
6 Papi
7 Ross
8 Salty
9 Aviles

I like this.
CC for leadoff. Let’s try. He will be able to do.
I know he don’t like to hit for leadoff.
But It’s huge waste of speed that teams put in CC behind Papi,youk,Adrian.

I think that the most problem is Where should CC hit  than Where should Jacoby hit.

Ells
Crawford
Pedey
Gonzo
Youk
Papi
Salty
Cody Ross
Iglesias

Ellsbury and Crawford should be well separated in the lineup, and neither of them can steal bases with slow runners in front of them.  Ellsbury will probably have a better OBP than Crawford.  That suggests Ellsbury 1st, Crawford 7th or even 8th.

Yes!  This is what the line-up should look like.

Ross (R handed) 7th with Salty (Lefty/Switch) 8th and Iglesias or Aviles (R handed) 9th…
keep the R handed hitters separated…but, top 6 looks great!!

1. Crawford
2. Peddie 
3. Jacoby
4. Gonzo
5. Youk
6. Ortiz
7. ross
8. Salty
9. aviles

I wonder what batter is less likely to ground into a double play with runners on base. If you 2 on and 1 out, who could you rather be hitting gonzo or ells? Do fast runners on base help break up the double play? Also, with men on base do you want a L/R handed batter? Do baseball players tend to pull the ball? Left handed hitters are already closer to first base. Hitting into the shift? or do you need to have a fast hitter? I’m all for putting peddie in either leadoff or further down in the line up to give it balance. And what about OBP, i was all for JD drew batting leadoff, but that wasn’t popular. Imagine ortiz or youk batting leadoff, or ninth for that matter. Its natural to have the sluggers in the middle of the order, but when their all on base do you really expect aviles or salty to deliver in the clutch? If crawford is uncomfortable at the bottom of the order, let him stay top 2. Some players are affected by battering order more than others. See: peddie as a cleanup hitter.

Also: if you see 3-4 players at bat in an inning, who do you want leading the following inning. I believe the right 3-5 player set is important, because your building innings. You want people that can take pitches, and people who swing. 

Jacoby is on base with one out, who do you want to hit behind him, a lefty power hitter? defensive shift? or a right hander with speed? if he’s on first, would they employ the shift on papi leaving 3rd base open for him to do a double steal? If ells is on 3rd, do you want a left or righty hitting? *(not that he’s going to steal home, unless its lefty) Also need to consider who they might intentionally walk depending on how you structure the order. 

Additionally, you have to think if it is a righty or lefty pitcher, and how that affects the batter. Do righties on righties pull more to left? hit it towards the shortstop? would of lefty pitching to a righty hit the other way more? dribble it to 1st or short?and consider where the pitchers back is turned to the base runners. A lefty pitching, its harder to steal second, but easier to steal 3rd or home.

If i was manager I would do:

1. Crawford
2. Youk
3. Gonzo
4. Ellsbury
5. Peddie
6. Ortiz
7. ross/sweeny
8. salty
9. aviles

Worst comes to worst, and you go 3 and out, you have ells starting off the 2nd with the bases empty and he can still steal. or you have 2 on- 2 out with peddie coming up, or loaded 2 out with ortiz. 

Game is on the line.. who do you want to hit with bases empty? and who do you want to hit with runners on? also, relief pitcher comes in, which three batter could make him throw 20 pitches. 

runner on first, who could score on a double by ortiz? not youk, not adrian, 

  I agree with Momster, but I’d flip Crawford and Ellsbury.